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Volumn 75, Issue 20, 2010, Pages 6820-6829

Furan approach to vitamin D analogues. Synthesis of the A-ring of calcitriol and 1α-hydroxy-3-deoxyvitamin D3

Author keywords

[No Author keywords available]

Indexed keywords

CARBONYL-ENE REACTIONS; CRITICAL STEPS; DI-ENOL; DIASTEREOSELECTIVE; DIHYDROFURANS; FRIEDEL-CRAFTS; HYDROXYALKYLATION; PETERSON OLEFINATION; PROPANAL; VITAMIN-D;

EID: 77957896650     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo101155c     Document Type: Article
Times cited : (16)

References (90)
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    • Vitamin D, 2 nd ed.; Feldman, D., Pike, J. W., Glorieux, F. H., Eds.; Academic Press: San Diego, 2005.
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  • 16
    • 1542533215 scopus 로고
    • For reviews of the ene and carbonyl-ene reactions
    • Arnold, R. T.; Showell, J. S. J. Am. Chem. Soc. 1957, 79, 419-422 For reviews of the ene and carbonyl-ene reactions
    • (1957) J. Am. Chem. Soc. , vol.79 , pp. 419-422
    • Arnold, R.T.1    Showell, J.S.2
  • 24
    • 17244369977 scopus 로고    scopus 로고
    • For a review of the use of BINOL in asymmetric reactions
    • For a review of the use of BINOL in asymmetric reactions, see: Brunel, J. M. Chem. Rev. 2005, 105, 857-897
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    • Brunel, J.M.1
  • 25
    • 0001842782 scopus 로고    scopus 로고
    • For studies related to the role played by the hydration of the molecular sieves in Ti-catalyzed reactions
    • For studies related to the role played by the hydration of the molecular sieves in Ti-catalyzed reactions, see: Terada, M.; Matsumoto, Y.; Nakamura, K. J. Chem. Soc., Chem. Commun. 1997, 281-282
    • (1997) J. Chem. Soc., Chem. Commun. , pp. 281-282
    • Terada, M.1    Matsumoto, Y.2    Nakamura, K.3
  • 60
    • 6444240772 scopus 로고    scopus 로고
    • The Au(III)-catalyzed Friedel-Crafts reactions of triflates or mesylates with electron-rich aromatic compounds may offer a more general solution to Friedel-Crafts cyclization reactions. See:;, In our hands, however, the cyclization of the triflate or mesylate of 4-(3-furyl)butan-1-ol under these conditions did not give the desired bicyclic furan.
    • The Au(III)-catalyzed Friedel-Crafts reactions of triflates or mesylates with electron-rich aromatic compounds may offer a more general solution to Friedel-Crafts cyclization reactions. See: Shi, Z; He, C. J. Am. Chem. Soc. 2004, 126, 13596-13597 In our hands, however, the cyclization of the triflate or mesylate of 4-(3-furyl)butan-1-ol under these conditions did not give the desired bicyclic furan.
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 13596-13597
    • Shi, Z.1    He, C.2
  • 61
    • 0026678562 scopus 로고
    • Although the intramolecular Friedel-Crafts reaction of 16 is mechanistically distinct from the intramolecular carbonyl-ene reaction of substrates used in the synthesis of the A-ring of calcitriol, there are some interesting similarities in the transition state. See
    • Although the intramolecular Friedel-Crafts reaction of 16 is mechanistically distinct from the intramolecular carbonyl-ene reaction of substrates used in the synthesis of the A-ring of calcitriol, there are some interesting similarities in the transition state. See: Kabat, M. M.; Lange, M.; Wovkulich, P. M.; Uskoković, M. R. Tetrahedron Lett. 1992, 33, 7701-7704
    • (1992) Tetrahedron Lett. , vol.33 , pp. 7701-7704
    • Kabat, M.M.1    Lange, M.2    Wovkulich, P.M.3    Uskoković, M.R.4
  • 88
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    • For recent examples
    • For recent examples, see: Camp, J. E.; Craig, D. Tetrahedron Lett. 2009, 50, 3503-3508
    • (2009) Tetrahedron Lett. , vol.50 , pp. 3503-3508
    • Camp, J.E.1    Craig, D.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.